Substituted tetrahydro-quinoline-sulfonamide compounds, their preparation and use as medicaments
a technology of tetrahydroquinoline and sulfonamide, which is applied in the direction of organic active ingredients, metabolism disorders, and digestive system, can solve the problems of food ingestion disorders, particularly obesity, and is a serious, fast-growing threat to human health, and achieves the effect of high affinity for 5ht6 receptors
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example 1
Preparation of 3-acetylaminophenol
[0134]
[0135]To a stirred mixture of 3-aminophenol (10 g, 91 mmol) and ZnO (8 g) was added acetic anhydride (10 mL, 92 mmol). The reaction mixture was stirred at room temperature for 15 min, dissolved in acetone (50 mL), the precipitate was filtered off, the filtrate was washed with acetone, and the solvent was evaporated in vacuo. The diacyl compound was dissolved in MeOH (130 mL) and after adding saturated solution of NaHCO3 the mixture was heated under reflux for 1 h. The solvent was evaporated in vacuo, the residue was acidified with HCl, and then extracted with EtOAc. The organic solution was dried and evaporation of solvent afforded crude monoacetylated compound (12.7 g) which was recrystallized from a mixture of CH2Cl2-MeOH (20:1). The precipitate was filtered and washed with CH2Cl2-MeOH until a white solid.
[0136]Yield: 11.5 g (83.6%); Rf=0.6 (CH2Cl2-MeOH 9:1).
example 2
Preparation of N-(2,4-dibromo-5-hydroxyphenyl)acetamide
[0137]
[0138]10 g (66 mmol) of the compound prepared in example 1 was dissolved in 200 mL MeOH and 700 mL CH2Cl2 was added. Benzyltrimethylammonium chlorobromate (2 eq, 45.7 g) was added during 1 hour, then the mixture was stirred for 15 min at room temperature (More reagent was added when necessary). The solvent was evaporated and to the residue water was added (500 mL). The mixture was extracted 4× with ether (1 L). After evaporating the solvent, the crude product was washed with CH2Cl2 to obtain brown-white crystals. Yield: 15 g (73.5%); Rf=0.47 (CH2Cl2-MeOH 19:1).
example 3
Preparation of 5-amino-2,4-dibromophenol
[0139]
[0140]A suspension of 15 g of the compound prepared in example 2 in 70 mL 30% HCl and 200 mL water was refluxed for 3 h. The suspension was neutralized with NaOAc. The precipitate was collected, the mother liquor was extracted with EtOAc, dried (MgSO4), evaporated. The collected products was washed 3× with water.
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